My friend Julia found a set of questions--I know not where--to designed to generate discussion. These were better than the usual ice-breaker things I have seen in the past, and did in fact generate some discussion in her chosen group via email and in person, especially when a little wine and good food was involved.
The one that gave me most pause was this: if you could take your twelve year-old self to lunch, what would she or he think of you and the way your life has turned out? Perhaps it's that I've reached middle age and I also have children around this age, but I had to really consider this idea.
My young self was living in a microscopic town in the Canadian hinterland and didn't know much beyond Friday night hockey nights, but she was lucky enough to be considered a "good kid" who babysat for people with university degrees and a world view outside the mypopia of life in a sleepy berg. (When I moved to bigger cities, I was shocked to meet people whose views were just as provincial, and realized that keeping the circle small allows most people to feel they belong, not to mention to keep tabs on where exactly they stand in the social pecking order.) But she was a practical girl and looked to the immediate next steps. I got the best grades I could, and managed to get into my dream school, Queen's University in Kingston, Ontario, which was only three hours away but might as well have been on another planet, since I was surrounded by kids from fancy Toronto prep schools whose fathers were diplomats and investment bankers.
It was my first experience with imposter symdrome, and overcoming it has served me well, since I've been able to scale the kind of career cliff I'd imagined, although I thought in those days that I'd be working in some sort of industry like publishing. I thank my lucky stars I didn't end up in that racket and therefore likely unemployed, but I did wind up working with really smart people from around the world and get to use my mind most days, so that's worked out rather well.
What else would my adolescent self asked me about? The fact that I'd gotten to Texas would have floored her, as it still does my older self at times. Where I'd traveled to would impress her, although I feel my two trips to Europe and most of the major cities in the US are pretty standard for most people I now know. I would be sure to tell her should time and money allow in the future, I've vowed to go further afield, and that she should do so before doing what is expected of her gets in the way.
She would also wonder about my romantic life and if I'd had a family. She envisioned a big life in work and then marriage much later, to an older man who would have already had a family. (I don't think she'd worked through how complicated this might be, but she thought of him as relatively unfettered and supportive of her work and intellect, a dream to be sure and not one I've yet to realize.) To know she had children might have horrified her early feminist sensibilities, although I could certainly assure her that it was the most satisfying thing I'd found to do.
She might also wonder if what I was doing made the world better in any way. Here I would express regret and urge her to do more. When I worked for a smaller company here in Fort Worth, I had time for volunteer commitments, but when I got into the global world and started commuting back and forth to Dallas (at least six hours a week on the road) it fell off my schedule. It's not that I feel guilty, exactly, but that I miss feeling I am part of my community. My children's school gives me a lot of that, but I don't do nearly enough to keep up my ties here. So what I would say is, figure out what you care about, and find the time to do it. You will get more from it than you give.
It's a good question for those of us who have become, in our minds, who we are: what did we expect to be, and have we achieved it? For me, the answer is almost all yes, although it reminds me how much more I have left to experience and learn.